Date Night
by Huntress79
Summary: It's the first date for all of them, but… oops, someone forgot to check the calendar first… Rated T mostly for the potty mouths of Dean and Gabe. Listed as a Dean/Cas story, but will contain lots of Sam/Gabe as well.
1. Chapter 1

Date Night

**Summary:** It's the first date for all of them, but… oops, someone forgot to check the calendar first…

**Notes:** Will contain several prompts from the E/O challenge. And since I can't write a story with just 100 words with the Winchesters for my life, I decided to give you that instead. Title is from the movie with Tina Fey and Steve Carell, but the story is not in the tiniest bit related to the movie plot. It's practically based on a song by Reinhard Mey, a German songwriter and singer, who really has a knack for describing life-like situations. Set in an all-human AU. Oh, and a big apologize to the inhabitants of the real Lawrence, Kansas, in case I got anything wrong with your sweet town.

**Extra-Note:** I sneaked in the titles of some TV shows. Extra virtual cookies to everyone who is able to find them.

**Disclaimer:** Do I really have to say it? _*looks up to see nods from Dean, Cas and Green Arrow, who just swept in*_ Okay, okay, I'll do it. Whatever you recognize in this little tale, it's not mine. Otherwise some shows would still be on, and on some other shows characters wouldn't have to leave. And I would have a bit more money at hand from the songs I used for inspiration alone.

* * *

Chapter 1 - Introduction

Lawrence, Kansas.

A nice little town right in the middle of nowhere and anywhere, surrounded by cornfields. And cornfields. And on top of that – cornfields. Its inhabitants were sure that they were the corn center of Kansas, but the not quite bigger town of Smallville, just a few miles north, claimed that title for itself.

But when you got to dig a little deeper, you could see that Lawrence was a bit more than just a regular Midwestern town. Sure, they had their typical joints, like Ellen's Diner or the old movie theatre or Seb's bar, but on the other hand they had some places they were sure not every small town had. Just like the pastry shop on the corner of Franklin & Bash, owned by Gabriel Milton, whom the townspeople pretty fast referred to as "the heaven-sent gift for the sweet teeth in town". Little did most of them know that Gabriel grew up in Lawrence, along with his brothers and sisters. But when Gabriel just had turned ten, the children's life took a wrong turn. Their mother, who really never got over the fact that her husband just left her one day, took off herself in a kind of religious fever and was never seen since then. Lucky for them, their Uncle Chuck agreed to have custody over the younger ones, including Gabe, Cas and Anna. The older kids, led by Michael and Lucas, were already on the way to their own lives, but they all stayed in town more or less. After a few years, when every search party for their mother came up empty, a judge wanted Chuck to have the kids' family name changed to his surname Shurley, but the dedicated writer wanted his nieces and nephews to keep the name Milton, since he didn't want them suffering from his less successful books.

But the Milton kids weren't the only kids in Lawrence who were met with a cruel change of fate. Only a few years after the Milton case, the young lives of Sam and Dean Winchester also took a dark turn. On their way home from a kids-free-weekend in a mountain retreat, their parents, John and Mary Winchester, died when their car crashed with a semi-truck only a few miles out of town. In the weeks following their funeral, both boys, five-year-old Dean and barely-a-year-old Sam, were centered in a juristic battle between Mary's relatives, the Campbells, and their appointed (by John and Mary in a written document of a last wish) guardian, Bobby Singer. And lucky for the boys, the judge took only one look at Samuel Campbell, the patriarch of the practically unknown family, and decided to keep the boys in town, in the capable hands of Bobby Singer and his neighbor Ellen Harvelle.

Over the years, Dean, Sam, Castiel and Gabriel met each other on several times. At first, Dean and Gabe really couldn't stand each other, but after a few clashes, they found they had something in common. First, both were big brothers, and as that, dedicated guardians to their little ones. Second, both grew up without their parents. And last but not least, they both had a sweet tooth. But while Gabe's one was not too picky about what kind of sweet treat (as long as it was all sugar), Dean had developed a special liking to all kinds of pie.

But not only had the elder brothers of the quartet some things in common, the younger ones had too. Both Sam and Cas were A-grade students, top of their classes and even had the opportunity to study at Harvard (Cas) or Stanford (Sam). But both declined and started their studies at the Kansas A&E instead. While Sam chose to go for a career as a lawyer (or as Dean had put it, to become one of the "Suits"), Cas enlisted himself in Psychology with a later specification on Children's Psychology. He knew first-hand what traumatic events can do to a child's mind, and so it was crystal-clear to him to help other kids with overcoming such events.

None of the four could pinpoint it, but somewhere along the road they all had fallen in love. Not with just anyone, but with one of their quartet. The big problem was that none of them could utter their true feelings. Dean was too much an alpha male, Sam was afraid of the reaction, Cas was too deep in his books to notice anything at first sight, and Gabriel… well Gabriel was too dedicated to his work that he also failed to notice anything. But thanks to some "playful" threats from Ellen, her daughter Jo, the three elder Milton brothers Michael, Lucas and Balthazar, and last but not least one Bobby Singer, all four of them managed to open their proverbial eyes at the right time. And so, after years of goofing and dancing around each other, Dean and Cas as well as Sam and Gabriel were heading for the preparations for their very first date.


	2. Chapter 2

A/N: Ok, here comes some real action. We follow the four boys in their preparations for the date and meet some of their friends and family. As for the coffee shop, just imagine the setting of the "Talon" from "Smallville", just with a tad more green. Oh, and the description of Dean during Sam's graduation is based on the photos from both the Comic Con and the CW Upfronts, where Jensen showed up in light grey *yummy* ;)

* * *

Chapter 2 - Preparations

Practically since the minute the two couples agreed on a date, the nerves of all four of them were strung like the strings of a guitar. They also agreed on some kind of a "war plan". Dean would take Cas first to the movies, then to dinner, and later come back to the Winchester's condo with him. Sam on the other hand would be picked up by Gabriel at home, and they would spend their first evening together at the Milton's home. But like with so many other things, it's all easier said than done, especially when none of them spared a look at the calendar. If one of them would have done, they would have realized that their first date was… exactly, on Friday the 13th. Piece of cake, isn't it?

But before they actually could meet, all of them had preparations to make. Bobby, owner of the local body shop, gave Dean the day off. Mostly because he was sure that his "son" wouldn't be able to get any serious work done that day. Since the boy had the proverbial wool over his eyes pulled off and declared his love for the younger Milton kid, everyone in town could see the change in Dean. Sure, he would deny it till the day he died, but they all were sure that he was getting softer at the edges.

And so late Friday morning, Sam woke up to Dean singing along to AC/DC's "Highway To Hell" in the garage. After selling their parents' house, the boys settled in a spacious two-store-condo right opposite Bobby's body shop, each store with its own entrance. A few years later, the house owner died, leaving the rest of the house to the boys. While trying to settle his own trembling nerves, Sam made his way to their shared kitchen, intended on getting a cup of coffee before facing his equally nervous big brother. A few minutes later, with two cups of steaming black liquid, Sam entered Dean's "sanctuary", the in-house garage with their only heirloom, a sleek black Chevy Impala 1967, bought by their father a few years before his marriage.

"Hey, Dean, thanks for the unique wake-up-call."

"I know. I'm a genius, right?"

"Yeah, whatever." He held up the cup. "Want some?"

"You really have to ask?"

Without waiting for an answer, Dean grabbed the cup, taking a large sip of his second-to-favorite beverage.

"So… today's the day."

"Geez, Sam, thanks for pointing it out to me. I totally would have forgotten it!"

"Liar."

"No, cross my heart." The look on his little brother's face told Dean otherwise. "Oh, come on, Sammy, I'm honest with you and you call me a liar."

"Dean, I know you my whole life, and I never saw you working so diligent on your "baby" when you had a date with anyone else."

"Wanna know why? Because Cas is not just anyone else. I don't know, Sammy, I mean, I'm not that great when it comes to emotions, but every time I see him or talk to him, I'm feeling…."

"…like your whole being is somewhere up in the clouds?"

"Yeah, but since when do you know how to end my sentences?"

"First, like I told you, I know you my whole life. But mostly, since I have the same experiences like you when it comes to Gabe. Remember when I was so focused on learning that you practically had to drag me over to the kitchen to eat?" Dean nodded. "Well, with Gabe, it's kind of the same. But in a total different way. He makes my mind, my heart feeling at ease, like a weight that has been lifted."

"Always knew that you were half a girl, baby brother."

"Oh. Yeah, and what about the heaps of SMS you sent to Cas and, accidentally, to me too? Wonder what they say about your personality."

"Bitch."

"Jerk."

And with that, Sam went back to his part of the condo, while Dean resumed both his work on the Impala's paint and his singing, this time to Metallica's anthem "Nothing Else Matters".

* * *

A few blocks away from the Winchester household, the neighbors were greeted with an almost similar sight. But while Dean worked on his "baby", Gabriel went through a seemingly neverending stack of cooking books. Sure, he was a Chicago-proved master of all kinds of sweet treats, but in all other departments of cooking the dark blonde man was quite at a loss. Thanks to Ellen, who not only took a pity on him by showing him some of her master skills in the kitchen but also borrowed him most of the books, he would be able to enchant Sam with a delicious meal straight from heaven. And thanks to Meg, his sous-chef at the pastry shop, he would have enough time to prepare.

"Looks like the tables have turned for once."

Seeing his elder brother practically shooting up in the air from his seat made Castiel Milton laughing so hard that he had to clutch his tummy. After all these years, he never would have thought that he would be able to do that.

"Well done, Cassie, but you know what day is today?"

Balthazar, the third inhabitant of the house, came up next to his younger sibling. Seeing them three together, you would never have guessed that they were actually brothers. While Gabe and Balty both enjoyed life to the fullest, Cas was the silent one, shy and not easily to crack open. Balthazar owned "Seb's bar", named after his favorite actor, a French guy named Sebastian Roché, whom Balty had seen on several TV shows.

"Of course, Balty. You really thought I would forget it?"

"Well, when it comes to your brain, you never can be sure."

"Amen, brother. Remember the summer between third and fourth year in high school…"

Used to the antics of his brother over the years, Cas prevented any further humiliation by putting a rag over Gabe's mouth, much to the amusement of Balty.

"All right, kiddos, I gotta go. Behave, have a nice day and an even nicer evening, and tell Dean and Sam I send my kisses. Oh, and if you need anything, you know where to find me."

Without waiting for an answer, Balthazar was out of the door, leaving his two stunned brothers in his wake.

"Did he really just encourage us on kissing the Winchesters?"

"Not really, Cas, he just encouraged us on doing more than that."

"Oh."

"Yeah."

* * *

Several hours later, time found the four knee-deep in the preparations. After doing some dire needed shopping (both Dean and Cas weren't happy about suits yet), the Winchesters retreated to their respective bathrooms, as well as the Miltons. Dean even bought himself a new cologne. And even though he laughed about it at first, the minute his nostrils took a smell of it, his mind promptly connected it with the image of a smiling Cas on one of the karaoke nights Balthazar had last summer. Damn it, he really had it with that man.

Cas on the other hand wasn't doing any better. He was reluctant at first when Michael showed up, insisting on taking his little brother suit shopping. Sure, he and Lucas, nicknamed "Lucifer", had to wear suits almost every day in their jobs at the big law firm and the bank, but that was something different. Cas still felt like a student, and students didn't do suits. Not when a good-hearted Fashion God invented such heavenly things like tight jeans and comfy sweaters, if even only for men like Dean Winchester. And other students on the campus Cas noticed in passing-by.

But now, as he was standing in front of his bed, clad only in a big towel, looking down on the new suit he had since that afternoon, he felt different. And that certainly had something to do with the image he couldn't get out of his head. Sam's graduation day. A bright, sunny day, topped by Dean… in a light grey suit. Maybe men were made for suits after all.

One floor below, Gabriel was finishing the last part of the main course of the menu. After a short talk to Ellen, he decided to settle on meals that could be prepared and be finished whenever they actually here. And God may bless her, the "surrogate" mother to both the Winchester and the Milton boys even offered to help him out and be there when he would go and pick "his" boy up. But Gabriel couldn't ask her for something like that. He was a grown up man, and "determined" was his middle name for a long time now. He would master it, of that he was sure.

* * *

Back at the Winchester condo, Sam's level of frustration reached a new level. For the better part of the last fifteen minutes, he tried to tie his new acquired tie, but to no avail. And so, with much grumbling under a non-existent beard, he knocked on the door to his brother's apartment – only to be greeted by a big brother who seemed to have a similar problem at hand.

"What's up, Sammy?"

"You need help with that?" Involuntarily, they both said it at the same time, causing them both to utter a nervous chuckle.

"Looks like we have a common problem?"

"Bobby?"

"No, not today. Definitely not today."

"Ellen?"

"Full house, no hands free, and even if she had her hands free, they would leave stains."

They were both silent for a few seconds before they seemed to come up with the only logical answer to their "problem."

"Jo."

* * *

Five minutes later, the boys were right in the middle of the "Arrow", the coffee shop in the old movie theatre. The place was busy as ever, but the petite blonde behind the main bar was some kind of a beacon of serenity amidst the chaos. As soon as she spotted them, she let out a shriek, causing most of the customers in front of the bar parting like a curtain when she made her way over to her childhood friends.

"Hey boys, what's up?"

"Don't you know that already?"

"Oh that. Yep, have heard about it." She led them over to a table next to the bar, which was set up for employees only. "So, you need some last-minute advice on how to proceed?"

"Thanks for the offer, sweetheart, but I think we're good", Dean answered with a dashing smile. Sure, they had been flirting at first, but when she realized Dean's true orientation they settled for being best friends instead. And Dean was glad to have her (and her mother as well) in his and Sam's life. If not for Ellen and Jo, the boys would have grown up without some female touch at all.

"So, what's the big buzz then?"

As if to answer her, both Winchesters held up their ties, causing Jo to fail at suppressing a chuckle.

"You guys really need help with that?" A double nod came from the boys. "Alright. You wait here, be right back." That said and done, she headed back to the employee's room, where some of her "girls" were gossiping.

"Hey, Ruby, Bela, I could use a hand out there. Special customers. Oh, and Lisa, feet off the table." Sometimes, Jo wondered what made her hire Lisa Braeden. Other than swooning for Dean, the brunette wasn't good for a lot of things. But that wasn't her worry right now. Following her two colleagues out to the shop, she already enjoyed the shocked faces of Dean and Sam when they would be face to face with their respective high school sweethearts.

"What the hell!"

Jo actually heard Dean before she saw him. He was on his feet, Sam as well, both ready to dodge out of the coffee shop.

"Dean, Sam, calm down. You both know for a long time that Ruby and Bela are working for me."

"And Dean, sweetie, we both know to where, or better to who, your hearts truly belong to."

Bela Talbot ended her sentence with a killer smile. Sure it was a big blow up in her face when she heard about Dean and Cas. But then again, she already knew back in high school that she and the elder Winchester weren't meant to be together. As much as her best friend, Ruby Delaine, and Sam weren't.

Not waiting for an answer from any of the Winchesters, both women stepped up, took the ties from the men, and within a very long heartbeat, had them tied properly around their necks.

"Now go and make your boys happy", Jo told the still stunned (and fuming) Winchesters with a big smile. "And when one of you is ready for the next step, the "Arrow" is ready when you are." And with that, she shooed them out of the coffee shop.

TBC


End file.
